Calendar of Events
Aug13Haunted Tours
Explore the SPOOKY side of Key West with a haunted historical tour.
Date: May 14, 2026 - December 31, 2026
Time: Thursday evenings (varies by operator)
Location: Off-Site (Key West – walking or trolley tour)
Aug13Key West Farmers Market
Visit the Key West Farmers Market every Thursday at the Truman Waterfront.
Date: May 14, 2026 - December 31, 2026
Time: Thursday's, 2:00 pm – 7:00 pm
Location: Truman Waterfront
Aug14Snorkel Experience
Dive into the 3rd largest coral barrier reef in the world and the only barrier reef in the continental United States.
Date: May 8 - December 31, 2026
Time: Friday's, varies by tour operator
Location: Off-Site (Catamaran / Key West waters)
Aug16World Class Fishing
The Florida Keys are known for amazing fishing. From the flats and shallows, sight fishing for permit, tarpon or bonefish or in the deeper waters of the backcountry, on the hunt for snapper, grouper or tuna.
Date: May 10, 2026 - December 31, 2026
Time: Sunday's, Varies by charter
Location: Off-Site (Florida Keys waters)
Sep03Just a Few Friends, Favorite Son Celebration
Just a Few Friends is a one-of-a-kind festival celebrating music, community, and island life in beautiful Key West over Labor Day Weekend.
Date: September 3 - 11, 2026
Time: Varies by event
Location: Key West (multiple venues)
Oct16Fantasy Fest
Fantasy Fest turns Key West into a spectacle of masked processions, parties, contests and dances attended by tens of thousands.
Date: October 16 -25, 2026
Time: Varies by event
Location: Key West (multiple venues)
Nov01Race World Offshore Championships
Experience the most powerful of water activities in Key West with the Race World Offshore World Championships.
Date: November 1 - 8, 2026
Time: Daytime (race schedule varies)
Location: Key West (Gulf side – six-mile course)
Jan26Mile 0 Fest
Experience the “friendliest festival” in paradise, featuring the best Red Dirt and Americana music at island venues, including Sunset Pier.
Date: January 26, 2027 - January 30, 2027
Time: All day
Location: Key West (multiple venues)
Apr28Key West Songwriter Festival
Discover the stories behind the songs at the world’s largest songwriters festival, featuring five days of live music, including shows at Sunset Pier.
Date: April 28, 2027 - May 2, 2027
Time: All Day
Location: Key West (multiple venues)
